April Iannazzone is a highly acclaimed marketing strategist and international business coach, but her most important job is being there for her amazing daughters Makayla and Talia and her husband Steve. After having virtually zero vacation time, leaving an empty seat at her girls' basketball games, and prioritizing job before family, April decided she'd had enough. Shortly thereafter, Self-Made Success was born! April now shows other burned out entrepreneurs how to finally achieve the freedom they once thought was impossible.


The gravest mistake a startup can make is to prolong scaling. Having grown her own business from a team of one, April couldn’t stress enough the long-term benefits and ROI that comes with assembling even a small team — whether it’s your spouse or an online freelancer. In her visit to MODERN ONTRAPRENEUR, the brilliant business strategist shared her team-growing advice along with her #1 lead generation tool.


0:34 - Identifying Missed Opportunities
From growing gyms to startups, April's unique skill set keeps her in business.

1:30 - Quizzes
​​​​​​April's #1 lead generation tool inspired by Tiger Beat Magazine

2:51 - Grow a Team Faster
Make the upfront investment to grow early. The ROI is nuts!

​​​​​​​5:15 - Delegation is a good start but...
Only by relinquishing some degree of control can you truly be free as an entrepreneur.

7:41 - Your Time on Your Dime
The biggest perk of entrepreneurship according to April

LR   Welcome to MODERN ONTRAPRENEUR. Today, we have April Iannazzone, who is a highly acclaimed marketing strategist and international business coach. After never having time to take a vacation, missing her girl's basketball games, and putting her job above her family, April decided she'd had enough. That's when Self-Made Success was born. April now shows other burned out entrepreneurs how to achieve the freedom they thought was impossible. Thanks so much for being here, April.
I grew a team of one, me plus one other person, and I put too much responsibility on that one person at the beginning. Grow a team that specializes in exactly what they need to do.
AI   Thank you so much for having me. I'm so honored.

LR   Good. Well, let's just dive into it. Tell me what you feel like is your most unique skill set and how that skill set has helped you in your success in business.

AI    Perfect. I guess, walking into a business or learning about a business, and really finding out what is working well for them and helping them scale that. More importantly, what opportunities are they missing out on.

LR Yeah.

AI   Really trying to figure out ... Maybe, I work with a lot of gyms figuring out, "Okay. What can you do other than that $100 monthly membership?" Create all different programs and expand online.

LR   Uh huh, so you've got kind of like a strategic mind for how to organize business and making offers it sounds like.

AI   Absolutely.

LR   Cool. You've grown your business for how long now?

AI    I have a few different businesses. The Self-Made Success, we're going into our third year. I also have an event production company and some other business, creative and alternative funding, things like that.

LR    Wow. What do you feel like is working right now to help grow those businesses?

AI      You know, my favorite thing right now is quizzes.

LR    Quizzes?

AI     Yeah. It's my number one lead generation for the majority of everything.

LR    Interesting. Tell me about how that works.
AI    Pretty much when you ... Well, maybe not you, but when I was younger there used to be Tiger Beat Magazine. You can answer about eight questions to find out if the boy really likes you.

LR   Oh.

AI     Everybody loves to do quizzes. When it pops up on Facebook, and it's "Do you have what it takes to become the next industry leader," or "Is your business leaving money on the table? Answer these eight questions to find out."

LR    It's an ad.

AI     It's an ad.

LR   Then, they click to it. Then, they go to your page, and there's a multiple choice.

AI    They answer eight quick questions.

LR   Then?

AI  Then, they go to one of three results pages.

LR   Got it.

AI   It's a quick video with me. If they answer one of the three questions right, they get the opportunity to get on the phone and have a strategy session.

LR   Awesome. That's the generation tool, and you're driving traffic through Facebook ads, and that's the thing that's blowing your business up right now.

AI    It's killing it for me at the moment.

LR   Unbelievable. That's great. Congratulations.

AI   It works very well with ONTRAPORT.

LR    Oh, good. You guys use ONTRAPORT. Awesome. As we look back on our time as entrepreneurs, we learn a ton. It's really easy for us to say to ourselves, "Man,
if I only knew then what I know now." What is that thing for you? If you could whisper in the ear of yourself five years ago, what would have made the biggest difference?

AI    Grow a team faster.
LR   Grow a team faster.

AI    Yeah, and make sure the team ... I grew a team of one, me plus one other person, and I put too much responsibility on that one person at the beginning. Grow a team that specializes in exactly what they need to do.

LR   Yeah, and how did that hurt you?

AI  It hurt me because it did stunt my growth a little bit at the beginning. I wasn't able to leverage as much, and I was still the one doing most of the work even though I was outsourcing a little bit.

LR    Usually for entrepreneurs, we don't grow a team, because teams are expensive. How would you recommend, again speaking to yourself back then, how would you have told yourself, "Hey! You need to have five people." How are you going to say for that?

AI    Yeah.

LR   How does that work?

AI  That's a great question because, actually, that's one of the things that most my clients say when I say, "Okay. You need this person."

LR   Yeah. They're like, "Are you going to pay for it?"

AI  Exactly. You need to make the upfront investment, because the return on investment is crazy big. If you can just picture your business in five years, where you want it to be in five years, I believe that's how you should make every decision.

LR   Yeah. The long view.

AI    The long view. The bigger vision.

LR   Would you recommend that entrepreneurs don't get started until they can afford to hire a team to create this thing?

AI   Oh, no. I think you should always get started.

LR    Just get started.
AI    Get started, but there's a lot of ways to find a team. Maybe your husband can do some stuff for you at the beginning. 

LR   Yeah.

AI    Go to Upwork.com. There's a lot of people that you can get on there as well. A lot of people try to barter, though, their team, and I don't think that's a good idea at all.

LR   Mm-hmm (affirmative). In terms, like for equity, you mean, or for -

AI   No, for like a -

LR    For like an energy exchange?

AI    For if somebody needs graphic design, and maybe they're a business coach. They would say, "Okay. I'll give you this much coaching, if you do my graphic design."

LR   Energy exchange.

AI  Energy, yeah. I do not recommend that.

LR   It doesn't work out. Pay real money for goods and services. Invest early, and look out for the long term.

AI   Absolutely.

LR   Yeah. Awesome. What's next for you? We always ... That's kind of like what you've learned. What do you want to learn next? What's the next most important thing for you?

AI    Oh, what don't I want to learn?

LR   Yeah. Well, tell me.

AI   You know? I'm like a sponge.

LR    What have you been learning lately?

AI    I think the next thing that I want to really perfect is speaking a little bit more. I speak all the time, but I am not the greatest speaker. I can admit that. That's one of the areas that I really want to grow in.

LR   Public speaking.

AI    Public speaking. Yeah.
LR   Yeah. What else?

AI   Good question. I guess, what else? I want to learn to give up a little more control. You know, that's a big one for me, even though I'm great at delegating and now building my team, I still want to have a hand on everything. I think that's something that I need to grow in.

LR    What's that going to get you, do you feel like?

AI    More time.

LR   Freedom.

AI    Yeah. It'll help me scale more, too.

LR   Yeah. Awesome. It's a huge challenge, because I mean, I definitely went through the pain of that myself. Especially, earlier on when we were between somewhere around 12 people was when it started to really get out of, I couldn't actually manage it anymore. Maybe it was even a little earlier, like seven or eight people. I really struggled from there to 25 to 30 people to let go of my baby. You know?

AI  Yeah.

LR    Let the results be what they are going to be, and somehow figure out how to successfully delegate has been a huge challenge.

AI    But you've done it masterfully, because you have such an incredible team. There's not one thing bad I can say about ONTRAPORT and the staff here.

LR   Yeah. We've definitely succeeded, but it wasn't easy is all I'm saying. It took us many years. Now, I'm definitely way on the other side of that, because I have no idea what's going on anywhere in my business.

AI  Yeah. That would drive me crazy, but that's where I need to grow.
LR   Tell me about the long term. What do you feel like you would like your legacy to be?

AI  My legacy is definitely, I work with a lot of women, it's definitely letting them know that they never have to depend on anybody else to support them. I mean, I went through a huge divorce and begging my husband to stay with me, because I was afraid I couldn't support myself and my children. My legacy is -

LR   Wow. That's impactful.

AI    Yeah. Letting my girls, my two daughters, and other women know that any point and time they can generate however much money they need.

LR   Yeah. That you can be self sufficient, and to have your kids really have a sense of confidence around their security and their futures.

AI   Absolutely. Yeah. Absolutely.

LR    Awesome. Beautiful. Well, we've called this series Modern ONTRAPRENEUR. We've launched this whole brand. What do you feel like it means to be a modern entrepreneur?

AI    Having a business on your own terms. Definitely. I'm able to build my business around the ideal lifestyle, and not in the fluffy word of lifestyle, but I'm able to attend every one of my kid's basketball games.

LR   Yeah.

AI    I work a few hours a day. I get a lot of work done, and maybe I have to work at night, too, but it's after the family stuff is done.

LR   Yup.

AI   If I want to go on vacation, I can go on vacation and work there. Definitely building a business on your own terms.

LR    Yeah. That's something that's different than entrepreneurship 20 years ago, you think?
AI    Even 15 years ago. Ten years ago, I owned a catering company. Completely different.

LR   Yeah, because you were just tied to it during all hours of the day.

AI   For everything. There was online marketing, but not as prevalent as it was now. Now, I work with people all over the world with the help of ONTRAport, of course. It's crazy how things have transformed so quickly in the business world.

LR  Yeah. The internet has really knocked the real-timeness out of the way we work in a lot of ways, so that you can organize your schedule any way you want to. Really be providing powerful services to people all over the place, huh?

AI   Absolutely.

LR   Yeah. Thank you so much for being here. Will you sign our wall?

AI    Absolutely. 

LR   All right.

AI   Thanks.